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Orlando had ambitions to get involved with the drug dealing aspect of the organization but his superiors needed him to keep a clean record for the clubs licensing. He approached D'Angelo Barksdale to try to involve him in cocaine dealing but D'Angelo refused and eventually told his uncle, Avon. Avon punished the wayward frontman with a humiliating beating.

Orlando was later arrested when he tried to buy drugs from an undercover Maryland State Police officer, and agreed to inform on Barksdale for the police. While imprisoned for the charge he was spotted by another inmate loyal to the Barksdale crew who phoned in Orlando's whereabouts. He was visited by Barksdale organization lawyer Maurice Levy, who was there to take his name off the club's license rather than offer help. Orlando was killed by Barksdale soldiers Wee-Bey Brice and Little Man in a botched sting operation which also resulted in the shooting of detective Kima Greggs.